Diethyl Malonate → Ethyl 2-Ethoxycarbonyl-4-(4-octylphenyl)butyrate

HRID 617875Notes

Reaction equation

HRID 617875 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28]I)=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:11]([O:10][C:2]([CH:3]([CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 105453621-(2-Iodoethyl)-4-octylbenzene

Product 1

HCID 21849265Ethyl 2-Ethoxycarbonyl-4-(4-octylphenyl)butyrateYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Sodium (2.67 g) was dissolved in absolute ethanol (100 ml) and diethyl malonate (18.6 g) was dropwise added thereto at 27-30° C. for 3 minutes. The mixture was stirred at 40° C. for 40 minutes and 2-(4-octylphenyl)ethyl iodide (40 g) was dropwise added to the reaction mixture at 44-45° C. over 10 minutes. The mixture was refluxed at 50° C. for 1 hour and stirred under heating for 1.5 hours. The reaction mixture was cooled and the solvent was distilled away under reduced pressure. Water was added thereto and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was subjected to silica gel column chromatography to give the subject compound (28.8 g).

Workup

  1. temperatureThe mixture was refluxed at 50° C. for 1 hour
  2. stirringstirred
  3. temperatureunder heating for 1.5 hours
  4. temperatureThe reaction mixture was cooled
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionWater was added
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThe solvent was distilled away under reduced pressure
  11. customthe residue obtained

Sources & evidence

ORD record
ord-f42d8f21eca04f609c9524370a65f15e
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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